4-Chlorobenzenesulfonyl chloride → 4-[5-(4-Chlorobenzenesulphonamido)pyrid-2-yl]-butanoic acid

HRID 1199675Notes

Reaction equation

HRID 1199675 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8](Cl)(=[O:10])=[O:9])=[CH:4][CH:3]=1.[NH2:12][C:13]1[CH:14]=[CH:15][C:16]([CH2:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23])=[N:17][CH:18]=1>N1C=CC=CC=1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:12][C:13]2[CH:14]=[CH:15][C:16]([CH2:19][CH2:20][CH2:21][C:22]([OH:24])=[O:23])=[N:17][CH:18]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 149896404-(5-Aminopyrid-2-yl)butanoic acid

Product 1

HCID 149896434-[5-(4-Chlorobenzenesulphonamido)pyrid-2-yl]-butanoic acidYield 35.6%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

4-Chlorobenzenesulphonyl chloride (1.17 g) was added portionwise to a solution of 4-(5-aminopyrid-2-yl)butanoic acid (1 g) in pyridine (15 ml). The resulting solution was allowed to stand at room temperature overnight when the solvent was removed under reduced pressure. The residue was dissolved in dilute sodium hydroxide solution (50 ml) and extracted with chloroform (4×50 ml) and the chloroform extracts were discarded. The aqueous layer was adjusted to pH=4 and was extracted with chloroform (3×100 ml). The chloroform extracts were dried over magnesium sulphate, the solvent was removed and residue was recrystallised from acetonitrile/water 1:1 to give the title compound (0.7 g) as white plates. m.p. 178°-180° C.

Workup

  1. customwhen the solvent was removed under reduced pressure
  2. dissolutionThe residue was dissolved in dilute sodium hydroxide solution (50 ml)
  3. extractionextracted with chloroform (4×50 ml)
  4. extractionwas extracted with chloroform (3×100 ml)
  5. dry with materialThe chloroform extracts were dried over magnesium sulphate
  6. customthe solvent was removed
  7. customresidue was recrystallised from acetonitrile/water 1:1

Sources & evidence

ORD record
ord-307cfec08ce442c59ad98770bc20b143
Source dataset
uspto-grants-1990_02
Patent number
US04902698

Reaction notes

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